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Boyfriend Test

Summary:

When Meg ropes Castiel into a job she found on craigslist of all places, he expected to just sit there with his phone and his alcohol. How hard could getting photographic evidence of Meg 'testing' a boyfriend's loyalty be? But then he actually sees Dean Winchester and decides that Dean deserves a boyfriend that doesn't look for weird strangers to test Dean's loyalties on freaking craigslist. If that potential new boyfriend happens to be Castiel, well. That's just fate then, isn't it?

Notes:

Inspired by a prompt on the Destiel profound bond discord server <3
Thank you to my betas Gomokie and SixofCups!

Work Text:

Boyfriend Test

Prompt By TakaLotti

“Clarence~” Castiel cranes his neck to look over the back of the couch at Meg’s sing-song call. He squints at her in question when she strolls in with a wide grin, brandishing her phone like it’s holding the secrets of the universe in one hand and a joint in the other.

Already dreading whatever that grin means, he turns back to watching the latest episode of Master Chef, not interested in whatever scheme she was cooking up this time. “Yes, Meg?” He asks, already only half paying attention.

“I need your help, angel o’ mine. I’ve just got the easiest, most lucrative job ever and I need a camera man.”

“No thanks,” He says flatly, snatching the joint out of her fingers and bringing it to his lips, “the last time you had a ‘lucrative job’ I had to bail you out of jail. And I’m still waiting for that $200 back.”

“This is different!” She plops down on the couch next to him, shifting to rest her feet on his lap as he takes a deep drag. “It’s not illegal at all.”

A ridiculous thing for her to say considering she was well aware it wasn’t the illegality he objected to, but the inevitable hassle her getting busted brings. For Heaven’s sake, he had a cupboard full of drugs and most of them are definitely not perscription. “Not illegal but morally dubious, I assume.” He poses it like a statement, because he already knows the answer.

“You wound me, Clarence.”

“Uh-huh.” He turns to give her a flat stare, a single eyebrow quirking up.

“Ok, yes, it’s morally dubious. But! For a good cause!” She offers up her phone, giving it a little wiggle.

“Money is not a good cause when it ruins my Friday night.”

She doesn’t reply, instead just shoves the phone right in his face and shakes it more aggressively. Sighing, he accepts it and pauses his show, adjusting his glasses so he can read the tiny print on the screen. He doesn’t get beyond Craigslist before he’s shoving it back at her. 

“No.”

“Just read it!” 

“Meg, I don’t need to read it to know one of us, probably me, will end up in an ice bath in some bathtub in a two star bed-bug infested motel. It’s Craigslist.

“You don’t need both kidneys anyway, Clarence.”

With a disgruntled groan he obliges, knowing she won’t leave him alone until he reads the damn ad. Really, he loves his best friend and roommate dearly, and he wouldn't trade her for the world or all the hunky dancers of that male revue they went to at the theater for his birthday. Their get-high and binge cooking shows night was the highlight of his week. But her predilection for Craigslist was dubious at best.

CL >South Dakota >Sioux Falls >Jobs >Gig Work

ISO Person to Test my Boyfriend's Loyalty – $100 Plus Bonuses (Central City)

Looking for an individual to help me test my boyfriend's loyalty this Saturday night. He’ll be attending his brother’s bachelor party at 7:00 PM. A picture of the applicant will be required to ensure they are my boyfriend’s type. I realize this is an unusual request, and I am more than willing to show proof of funds. Payment through one of the following apps: Zelle, Cash App, or Venmo.

Candidate Requirements:

  • Age: 25 to 40
  • Gender: Any (my boyfriend is bisexual)
  • Appearance: Preference for dark hair and light eyes
  • Conventionally attractive
  • Ready and willing to flirt
  • Confident
  • Discreet
  • Reliable

Compensation is $100 upfront, an additional $50 drink tab, with additional pay for the following:

  • $50 he accepts a drink from you
  • $100 he dances with you
  • $200 he kisses you on the cheek
  • $200 he sit on your lap
  • $500 he kisses you on the lips
  • $500 gives you his phone number
  • $750 he makes out with you
  • $1,000 you go home together

To receive bonuses you must provide video or photographic evidence obtained personally or through a third party observing. Evidence must be provided before additional pay is given.

Serious inquiries only. I love my boyfriend and am considering asking him to marry me, but I must ensure his loyalty and dedication first as I am a small business owner.

Castiel slowly lowers the phone, turning to stare blankly at Meg and her shark-like grin. “You have got to be kidding.”

“No!” She snatches the phone back. “I’ve already messaged the guy, it’s legit. Apparently he thinks his boyfriend is sluttin’ around cause he used to be a hoe or some shit.”

Sluttin’ around, huh?” He snorts and rolls his eyes, turning his show back on and pointedly cranking up the volume. “Just another person concerned about their bisexual significant other sleeping around behind their back. I wasn’t aware you held such reductive views on bisexuals.”

“You know I don’t. But seriously, Clarence. Worst case scenario I get to fuck a really hot guy, save this dude from a cheating boyfriend, and make over a thousand bucks. Best case? Guy’s an angel and tells me to go fuck myself and I’m still a hundred bucks richer and full of tequilla.” 

“Still, no thank you.”

She pokes him in the side with her perfectly pedicured toes, raising her eyebrows as she darts forward and snatches the remote from his hand and turns off their show. “Half of that easy money and booze could be yours.”

“I’m not that desperate for money or alcohol, Meg.”

“Sure, but just think! We could go on vacation or something. And if we get that other shit too? That’s over three grand!”

Castiel frowns, considering. It had been a significant amount of time since he’d last gone on vacation… Before college, probably. Which is over a decade ago now. He sighs, relenting. “Alright. Half for me, and I don’t have to talk to anyone. And you buy my drinks and refill the pot supply.”

“Hell yeah, Clarence.” Grinning like a mad woman, she types away vigorously on her phone, holding it up to snap a quick selfie. “This is going to be fucking great.”


The Roadhouse is a dive bar and Castiel already wants to leave. It smells like stale beer, salted peanuts, and low income desperation. He wrinkles his nose, stripping off his trench coat as he heads towards one of the few empty tables with Meg. The place is crowded with a single (obviously overworked) blonde waitress rushing table to table filling glasses. And there’s so much flannel.

“Alright, so what does this disloyal boyfriend look like?” Castiel asks dryly, looking around the room in disinterest, eyes scanning for anyone who looks like they may be the groom-to-be, assuming their target might be lingering near him.

Meg fishes her phone out of her purse and passes it over to him. Castiel is so shocked by how devastatingly beautiful the man grinning on the screen is that he fumbles the phone and nearly drops it. He looks like a male model or a dashing lumberjack. Swallowing, he pulls it closer to his face, inspecting the man’s lovely visage. “He has freckles.”

Castiel was not prepared for this man to have been crafted just for him in the clouds of heaven itself. A strong jaw with just the perfect amount of stubble, sharp and mischievous green eyes, soft looking lips and a cocky aura of confidence. He wants to take this man apart with his tongue.

Slowly, Meg turns to look at him, raising a single eyebrow as she narrows her eyes. Her too-knowing gaze takes in the slight blush that’s raised to the apples of Castiel’s cheeks and a devious grin inches itself across her face. “See something you like, Clarence?”

He licks his lips, peering around the bar with renewed interest. For fuck’s sake, he’d have to be blind not to see something he liked. His damn wedding, white picket fence, 2.5 kids, and a damn dog were in that picture. Shamelessly, and with his usual style of bluntness, admits, “Yes.”

She bursts out laughing, “Clarence! You dog.”

“What? Obviously our employer doesn’t trust his boyfriend.” He cranes his neck, squinting at the bar where he sees a tall, dark blonde haired man standing next to the tallest person Castiel has ever seen. That could be him, so he turns back to Meg’s phone, helping himself to her email to check the correspondence with this Benny man. Oh. His future husband’s name is Dean. It fits him perfectly.

“And you’re just helping the poor thing upgrade to a better model, right?” Meg snickers, getting comfortable in her chair, gracefully accepting the fact that she’s no longer the one getting laid tonight.

“Of course.” Satisfied and with target acquired he stands, smoothing out his sweater vest, abruptly wishing he had chosen something a little more attractive and a little less nerdy. At least he was wearing his good slacks. Humming to himself he rolls up his sleeves to reveal his forearms and ruffles his hair a little to get the artfully mussed ‘sex hair’ his previous partners had been obsessed with.

“How charitable of you, Clarence.”

“Mhmm. Would you mind terribly, Meg?” He motions to her phone and pockets it just in case at her dismissive wave and passes her his own instead. “I don’t see why we can’t still get paid while also getting me a new boyfriend.”

Meg snorts out a laugh, shooing him away, “Go get ‘em lover boy.”

With a nod Castiel strolls over to the bar, taking a seat near the lovely blonde man, keeping half an eye on him while he orders a whiskey to nurse while he observes his pretty prey. From what he can see over the next half an hour, Benny’s worry was totally unnecessary, Dean wasn’t paying attention to anyone but the grinning man in a tiara and glittery groom sash.

He waits patiently until Dean is finally alone before making his move, taking his glass and strolling over and motioning to the stool next to him. “Is this seat taken?” Out of the corner of his eye he can see Meg with her phone out, pretending to text as she laughs to herself.

Dean turns and, oh, he’s even more beautiful in the flesh. Verdant green eyes blink up at him, briefly flickering up and down his body in what Castiel hopes is interest. He gives him a shrug accompanied by a charming, lopsided grin, “Nah man, feel free.”

“Thank you.” Castiel makes a show of looking around, motioning with his glass and a finger towards where Dean’s brother is doing shots with a group of rowdy people in ballcaps and more flannel. “Are you a friend of the groom?”

“Nah, that’s my little brother.” Dean visibly perks up, pride coloring his cheeks, his boyish grin near blinding. “He’s getting married next week. You know, in case the sash didn’t make it obvious.”

“That’s wonderful. I’m Castiel, by the way.” 

“Dean.” When Castiel takes his hand for a friendly shake he’s pleased by how warm and calloused and confident Dean’s grip is. He has a working man’s hand. The hand of someone who definitely needed to be taken care of. By Castiel, specifically.

“Can I get you another one of those to celebrate, Dean?” He motions to Dean’s beer, head cocked to the side with an inviting smile.

Dean blinks for half a second before his eyes widen, evidently surprised by the offer. Perhaps the bar’s regulars knew he had a boyfriend already. “Hey, sorry man I’m flattered, but I got a boyfriend, you know?” 

He offers Castiel a bashful, consoling smile and he is delighted. Just as he suspected Dean was loyal to his boyfriend. Not that he felt any guilt about absolutely ripping that relationship apart at the seams and whisking Dean away to brighter pastures. Dean would be better with him, anyway. The beautiful man didn’t need a boyfriend that was asking strangers on craigslist of all places to test his loyalty. 

“Benny, right?”

“Uh… yeah.” Dean frowns at him. “You knew I got a boyfriend and you still tried hitting on me? Kind of a dick move, man.”

He takes out Meg’s phone, opening the email chain with Benny. “He’s the one who told me to do it.”

“What?”

Castiel hands the phone over to a bemused Dean who stares at him for a second, eyebrows furrowed at the sudden change of events before slowly looking down at the phone. The confusion slowly morphs to disbelief which bleeds into anger the more he scrolls down. “What the actual fuck.”

“I’m terribly sorry about this.” And he is, Dean shouldn’t have to put up with a suspicious boyfriend sending strangers after him.

“Man, what a fucking dick. He cheats on me with fucking Andrea and then has the fucking balls to do this shit?”

It takes a moment for Dean’s words to sink in and when they do Castiel feels a sharp burst of rage ignite in his chest. Of all the hypocritical… It takes all of his willpower not to growl in disgust. How could anyone have a lover like this Adonis and cheat on him?

He takes a breath to calm himself. “I’m so sorry…” he murmurs, resting a hand on Dean’s shaking fist. “You seem lovely. You don’t deserve to be treated like that.”

“I can’t believe that asshole. Man, fuck him. Fuck him.” Dean scowls down at Meg’s phone, voice trembling. With an audible snarl of rage (and oh does that sound do things to Castiel), Dean fishes in his back pocket for the oldest flip phone Castiel has ever seen. “I’m going to call that fucker and bitch his damn ass out.”

Castiel clears his throat, raising a hand and gently halting Dean’s movement. “If I may suggest something…?”

Dean glances up at him, eyes still flashing with beautiful, righteous anger and Castiel has to stop himself from lurching forward and capturing that perfect scowling mouth in a wild kiss. Patience, Castiel. “What?”

He gestures at the phone, “Your boyfriend, or, well, ex-boyfriend…?”

“Yea, he’s definitely my fucking ex, man.”

“Right, right. So, he’s going to pay my friend Meg and I for being here. That’s her, over there with the phone clandestinely taking pictures of us.” He points over at Meg, Dean turning to look, eyebrows raising as Meg wags her fingers at them and making an unflattering kissy face. “I don’t see why we can’t bleed him dry before you dump him.”

Dean stares at him for a long moment, a crease between his brows as he considers Castiel’s words, worrying his bottom lip between his teeth. “You’re thinkin’ we should check off some shit on his list.”

“Yes.”

To his surprise Dean laughs, shaking his head. It’s a beautiful sound, deep from his belly, laced with amusement and thankfully not self-deprecation. “Shit. This has to be the weirdest way someone’s asked to take me home ever.”

Castiel can’t help but chuckle too, eyes bright as he leans in. He lets his tone drop to a deep rumble, resting his hand on Dean’s knee high enough to convey the sincerity of his next words without being overly aggressive. “Well, I must admit, I certainly wouldn’t be opposed to that. You are exceptionally beautiful, Dean. And quite charming.”

Dean’s head cocks slightly to the side as he considers Castiel, an amused smirk threatening to jerk the corner of his lip up, “You flirtin’ with me Cas?”

“Of course. I would be remiss to pass up on the opportunity.”

“Alright, Romeo, woo me. But just so you know, I’m not a cheap date.” Dean winks flirtatiously and Castiel grins, wide and toothy. “And you can tell your friend she can come over. Kinda creepy she’s over there spying on us like some stalker. She’s one trip to the dollar store away from wearing a felt mustache”

Castiel laughs at that, turning and motioning Meg over with a casual wave of his hand. He gives her a pleased smile and a covert thumbs up as she sits next to them. “Meg, this is Dean. Dean, this is my best friend Meg.”

“Hey Meg, I hope you’ve been catching my good side.”

Meg snorts out a laugh as she takes Dean’s offered hand, giving it a shake. “I take it you spilled the beans, Clarence?”

“Mhmm. We’ve decided to join forces to drain Benny’s bank account as recompense for being a hypocritical cheat.”

“Oh fuck, what a dick! Shit, let’s get all that dude’s money. First thing on that list was getting Dean here to accept a drink, right? Lemme get a good angle.”

Meg and Dean get along like a house on fire, trading sharp quips and barbs, and Castiel is extremely pleased to see his best friend and the love of his life (and soon to be husband) getting along so well. They’re having way too much fun hamming up their interactions for Meg as she goes into several dramatic angles to capture their ‘first interaction’ where Dean accepts a glass of whiskey. Eventually they settle themselves down, taking a proper little video, though by the time they get the first box checked on their list they’ve drawn a bit of an audience. Including Dean’s brother, who wanders over with a bemused frown.

“What uh, what’cha doin’ Dean?”

“Hey, Sammy. Just scamming Benny,” Dean says casually, leaning into Castiel’s space to plant a kiss on his cheek while Meg snaps pics from a few different angles. “Dude sent these guys to try and catch me cheatin. Can you believe that shit?”

“Seriously?” Sam’s face goes an indignant red as he sputters out, “After that shit with Andrea?”

“Dude, that’s what I said!”

“I knew that guy was a dick. But this is beyond messed up.” Sam shakes his head with a scowl.

“Yea, right? Oh, yea, fuck, this is Cas, and that’s Meg, by the way.” Dean pauses to motion at Castiel, who inclines his head and offers a handshake, and Meg who’s busy downing another shot of something neon green. 

“Hey man, nice to meet you.” Sam’s grip is just as strong as Dean’s, though not nearly as calloused. A scholar’s hands, perhaps, or a white collar worker. Sam had the air about him of some fort of formal learning.

“Likewise, Sammy.”

Sam groans, “Just Sam is fine. Only this asshole calls me Sammy. So uh, what’s with the…” he motions at Meg and her phone.

“Benny wanted them to catch me ridin’ dirty, said he’d give ‘em a bunch of cash to play paparazzi of me hoein’ around.” Dean shrugs, a smug grin settling on his face. “So we’re going to give him what he paid for.”

Sam nods approvingly, “Alright, well, don’t forget we got breakfast with Mom and Dad tomorrow, so don’t get too wasted.” 

“No promises, Sammy.”

The three of them have an absolute blast. Dean fits into the Castiel and Meg dynamic perfectly, like he’s been with them all along, and his friends are surprisingly enjoyable to be around too. Even the Roadhouse itself is growing on him and Castiel regrets his snobbish initial reaction. It’s incredibly easy (and enjoyable) to rack up the extra cash Benny offered, dancing and kissing the night away.

And by God, Dean is an excellent kisser. He’s all firm hands and skilled tongue sliding against his own, their mouths fitting together just as perfectly as Castiel had imagined the first time he saw Dean’s face. Somewhere nearby he knows Meg is still recording this, but he’s beyond caring now, too invested in capturing Dean’s bottom lip in his teeth and tugging. Dean makes an absolutely delicious moan and it is time to go. 

“You wanna get outta here?” Castiel purrs against his mouth, peppering kisses across his cheek to his neck.

“Fuck yea,” Dean practically jumps up, grip tight on Castiel’s hand, “your car or mine?”

They pass Meg and her phone on their way out, hand in hand, staring at each other hungrily. “Yours. My friend drove me.”

Somehow they manage to make it to the parking lot where Dean’s parked his car, a magnificent black beast of a thing, and if Castiel wasn’t so busy shoving Dean up against the side so he could devour his perfect, pretty mouth he might have paused to appreciate it. As it is, they’re both preoccupied, Dean barely getting the doors unlocked before they clamber into it.

Castiel is sure they’re speeding and definitely driving dangerously, but he just doesn’t care when Dean’s trembling under his hands while Castiel sucks bruises into his neck. 

“Fuck, Cas, you’re going to make me crash.” Dean gasps out when Castiel’s hand slides over Dean’s thigh, inching towards the bulge straining the front of Dean’s jeans.

“Mmm, you better hurry up before I do something to really distract you,” he purrs in response, palming Dean’s cock. “Like lean down and blow you right here.”

He chuckles darkly against Dean’s fluttering pulse as the other man gasps out a wrecked ‘fuck!’ when Castiel squeezes and rubs. The wheel jerks for a moment and makes them swerve, and if Castiel wasn’t so damn horny right now, he’d be thankful the road was empty this time of night.

They arrive at Dean’s little house without wrapping themselves around a tree and only one of Castiel’s hands down Dean’s pants.They don’t get further than that before Dean is fumbling to turn the car off with trembling hands and throwing himself at Castiel. It’s awkward in the front seat, elbows and knees banging into glove boxes, steering and shifter sticks but it’s raw and hot and Castiel wouldn’t mind fucking Dean right here even at the price of a jacked up back in the morning.

But Dean still seems to have some semblance of sanity, pulling away and practically stumbling out of the car, dragging Castiel along up the path to the house and shoving him inside as soon as the door is open. Despite Castiel’s best efforts to devour Dean right there against the door, they manage to make it to the living room couch, tumbling down together onto the cushions.

They scramble to undress each other between bites and kisses and ravenous mouths claiming unmarked flesh. Castiel leans back just long enough to take in the expanse of Dean’s beautiful tanned skin. He’s delighted to see the freckles continue along Dean’s shoulders and he’s desperate to see where else those freckles are.

And then they’re unable to keep themselves apart a second longer, crashing together in a flurry of tongues and teeth. They rut together there on the couch, Castiel gripping Dean’s naked thighs hard enough to bruise and hiking them up over his hips so he can grind down against him. Their bodies slot together perfectly, Castiel settled between perfectly bowed legs, cocks pressed and leaking between stomachs as they writhe together filling the room with grunts and moans.

It’s rushed and sloppy and messy and perfect, everything Castiel ever wanted and didn’t know he needed. Dean ignites a fire in him in a way no other partner has, turning Castiel damn near feral in his desperation. When Dean comes with a sob of pleasure Castiel is powerless in the face of such transcendent beauty. Dean is perfect in his orgasmic bliss, body bowing off the couch under him, arching into Castiel’s embrace while painting their bellies in thick stripes of white that quickly get smeared in Castiel's desperate chase to find his own release.  When his own orgasm hits, it’s a near violent onslaught of white-hot pleasure, crashing through him so hard and fast it rips his breath straight from his chest. 

He collapses against Dean, draping over him as they both struggle to catch their breath, sticky and satisfied.

“That was… Holy fuck.” Dean is the first to gather what’s left of his wits, laughing out shakily with an exhausted, sated grin.

“Mmm.” Castiel agrees, managing to huff out a breath of laughter as he rests his forehead against Dean’s, pressing soft, fluttering kisses over his flushed face.

“So uh…” Dean grins at him, beautiful and pink and sweaty and Castiel’s,  “What’cha doin’ tomorrow?”

“More of this, hopefully.”

Dean obviously approves of this plan if the messy kiss is any indication. 

Castiel stays the night (and will do the same every night after that, if he has his way, which he most assuredly will). When dawn breaks, they wake to the morning light, cuddling on Dean’s luxurious memory foam mattress, a tangle of limbs and lazy kisses. With a yawn, Dean grabs his phone, sending off the usual ‘morning handsome <3 breakfast?’ text to his ex-boyfriend, making plans for ‘their’ favorite cafe.

Devious plan complete, he leans over and gives Castiel a big, open mouthed wake-up kiss. Dean wraps around Castiel like an over-friendly octopus, and to be fair, this is a wonderful way to wake up even if it just makes Castiel want to burrow in bed forever. “Come on, sleepin’ beauty. You wanted to be there for Benny’s walk of shame. We gotta be there in an hour.”

Castiel considers his options and a single perfectly blue eye cracks open, “...Maybe you should just ghost him.”

“Yea, I’m sure Meg will totally not try slashing my tires if we don't show.”

True. Meg hated mornings even more than Castiel did, and would definitely be on the war path if they failed to arrive while she was there, eagerly awaiting the drama of a public spectacle at Cup de Grâce. An ironic name, considering their plans today. 

So, fear of Meg rousing them from their comfort, they head off to shower and get ready (nearly losing track of time getting dirty under the hot water spray and having to get clean… again).

They arrive just in time, Castiel going in first, Dean planning to wander in five minutes later so as not to look suspicious. Meg grins at Castiel from a table near the window and he drops into the seat next to her, pulling the offered coffee cup to his lips with a sigh of relief. When he finally gets an eyeful of her ridiculous outfit he chuckles. “Aviators and a trench coat, Meg? What are you, deep incognito?”

She ignores his quip and grin. “Just got the cash.” She waggles her phone and then casually motions to a man nearby with it.

Castiel shifts in his seat, letting his eyes slide over to Dean’s now ex-boyfriend. The man doesn’t look like someone who would post ads on Craigslist, he looks so regular and nondescript that he has to wonder what drew Dean to him in the first place. He’s stockier, more than likely by build than fat if Castiel had to guess, with well trimmed stubble, a newspaper cap, and honest to God suspenders.

When Dean finally walks in, heading towards Benny, the man speaks for the first time, “Mornin’, cher.”

Oh, okay, the accent was probably the draw. It wasn’t Castiel’s cup of tea, but he supposes he can see the appeal.

Dean is a marvelous actor, going up to his ex and kissing him on the cheek before settling in the only other chair at the small table, “Morning, Benny.”

“Did you have fun at your brother’s bachelor party?” Benny is apparently right to business, reaching into his pocket and drawing out his phone.

“Oh yea, it was a great time man. Shame you couldn’t make it, Ellen and Jo would have loved to see you.” He takes out his own phone, all bright tooth grin. “Don’t worry, I got a ton of photos.”

Benny frowns at that, “Dean. I know what you got up to last night.”

Dean makes a wonderful show of being confused and then shocked when he takes Benny’s phone, scrolling through the ‘incriminating’ pictures and videos Meg had sent last night. “Benny… I…”

“I can’t believe you would do this, Dean.” Benny sounds so hurt that Castiel nearly snorts coffee out his nose in disbelief.

“Well, in my defence, I was already single at the time.”

The hurt is immediately wiped from Benny’s face and replaced with a nervous confusion as Dean passes his own phone to him, a forwarded copy of the email correspondence and a payment confirmation already pulled up.

“See,” Dean says, speaking a little louder, drawing eyes from nearby tables.

“Cher,” Benny whispers sharply, glancing around anxiously, and Castiel feels a smug sense of satisfaction watching the asshole squirm. “Maybe we should go home, do this in private—”

“Nah,” Dean cuts him off, and bowls right over him, “man, I was so pissed when you cheated on me with Andrea, little miss not someone you have to worry about, Dean, we’re definitely over. But I forgave you, because shit, we’d been together four years man. Four fucking years. And I figured, hey, one little mistake ain’t bad. But then I have this interesting conversation with this absolute angel at my brother’s party last night.”

“Dean, please, you have to understand—”

“That apparently my boyfriend had posted an ad on fucking Craigslist of all places, trying to pay someone to flirt with me and try and fuck me. And I’m like, what the actual fuck, man? Craigslist is full of freaks and stalkers and shit, what if this random dude tries to hurt me? Or assault me? Or any of the other fucked up shit people that answer Craigslist fucking ads do, right?”

Dean,” Benny whimpers, actually whimpers, sinking into his chair, “that wasn’t my intention, I…”

“And then I thought, what the actual fuck? He has the balls to cheat on me and then tell some stranger he’s worried I’m going to be fucking around because, and I quote, I ‘had a bit of a history with slutting around.’ Which holy shit dude, fucking hypocritical much?”

Benny doesn’t even respond at this point, staring down at the table, face red in shame and embarrassment.

“And then, this gorgeous fucking angel is like, Dean, we should totally scam your shitty ex-boyfriend and bleed him dry. And I figure you know what, fuck him, right? So yea, we make out, dance, I sit on his lap and flirt and we walk off together suckin’ face while his friend records us for ‘evidence.’”

“So you didn’t actually…?” Benny sounds hopeful now, like he has any chance of salvaging this shit-show. Castiel takes a sip of his coffee, smirking as Meg snickers next to him.

“Oh no, I definitely took him home and we fucked the ever living shit out of each other.” The waitress who had been coming over to Dean and Benny’s table to refill coffee abruptly spins on her heel and goes off the other way at Dean’s blunt admission. “I also upgraded to a new boyfriend who just scammed my shitty, cheating ex out of three grand and doesn’t ask people on Craigslist to fucking stalk me.”

With that Dean doesn’t give Benny even a chance of answering, just stands and flips him off, strutting over to sit with Meg and Castiel who are, indeed, three thousand dollars richer.

“We should totally go to the Maldives,” Meg says as soon as he sits, turning her phone to show him a fancy ass hotel.

Castiel smiles as he flags the waitress down for a refill, ignoring the sad kicked puppy look Benny keeps sending in their direction, enjoying Meg and Dean arguing about the benefits of Hawaii versus the Maldives on a spiritual level. Dean fits in with them absolutely perfectly, like a missing puzzle piece he didn’t know he misplaced, and Castiel can’t remember the last time he felt this damn happy without being stoned six ways to Sunday.

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